DE67923C - Process for the preparation of the p-amidobenzoic acid esters of guaiacol and eugenol, as well as the acetyl derivatives of these esters - Google Patents
Process for the preparation of the p-amidobenzoic acid esters of guaiacol and eugenol, as well as the acetyl derivatives of these estersInfo
- Publication number
- DE67923C DE67923C DENDAT67923D DE67923DA DE67923C DE 67923 C DE67923 C DE 67923C DE NDAT67923 D DENDAT67923 D DE NDAT67923D DE 67923D A DE67923D A DE 67923DA DE 67923 C DE67923 C DE 67923C
- Authority
- DE
- Germany
- Prior art keywords
- esters
- guaiacol
- eugenol
- preparation
- well
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- RRAFCDWBNXTKKO-UHFFFAOYSA-N Eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 title claims description 14
- LHGVFZTZFXWLCP-UHFFFAOYSA-N Guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 title claims description 12
- 239000005770 Eugenol Substances 0.000 title claims description 7
- 229960002217 Eugenol Drugs 0.000 title claims description 7
- 229960001867 Guaiacol Drugs 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 title claims description 3
- 150000002148 esters Chemical class 0.000 title description 9
- 239000002253 acid Substances 0.000 title description 5
- 239000011780 sodium chloride Substances 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 4
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-Nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 claims description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N Phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- JYMVSZGJZRQOFY-UHFFFAOYSA-N (4-nitrobenzoyl) 4-nitrobenzoate Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)OC(=O)C1=CC=C([N+]([O-])=O)C=C1 JYMVSZGJZRQOFY-UHFFFAOYSA-N 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- -1 hydroxyl hydrogen Chemical compound 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000001225 therapeutic Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000003638 reducing agent Substances 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Chemical group 0.000 description 2
- 239000011734 sodium Chemical group 0.000 description 2
- YHRILHYQNVLOEQ-UHFFFAOYSA-N (2-hydroxy-5-nitrophenyl)-phenylmethanone Chemical class OC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 YHRILHYQNVLOEQ-UHFFFAOYSA-N 0.000 description 1
- GRNCTJVYPJXPAY-UHFFFAOYSA-N 2-methoxyphenol;sodium Chemical compound [Na].COC1=CC=CC=C1O GRNCTJVYPJXPAY-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P Ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 230000036826 Excretion Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J Tin(IV) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 238000010192 crystallographic characterization Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
J. D. RIEDEL in BERLIN.J. D. RIEDEL in BERLIN.
der Acetylderivate dieser Ester.of the acetyl derivatives of these esters.
Der innerliche Gebrauch desThe internal use of the
(1J
(2) ( 1 y
(2)
Eugenols C6H3-OCH3 ^OH Eugenol's C 6 H 3 -OCH 3 ^ OH
Guajacols C6 ± j.^ ^ ^ „
und desGuajacols C 6 ± j. ^ ^ ^ "
and des
(0
(3)
(4)(0
(3)
(4)
bei tuberkulösen Erkrankungen hat sich seit langem vortheilhaft bewährt. Zu gleichem Zweck sind auch Ester dieser Phenole, besonders der Benzoesäure- und der Zimmtsäureester, therapeutisch angewendet worden. Bei Verwendung dieser Ester wurde jedoch von verschiedenen Seiten der Uebelstand hervorgehoben und bezeichnet, dafs dieselben nur schwer und unvollkommen im Organismus spaltbar sind und daher die beabsichtigte Guajacol- bezw.Eugenolwirkung nicht voll zur Geltung bringen. Dieser Uebelstand läfst sich völlig beseitigen und werden Körper von werthvollen therapeutischen Eigenschaften erhalten durch Einführung einer in Parastellung befindlichen Amidogruppe in den Säurerest der genannten Ester.in tuberculous diseases has long been shown to be beneficial. For the same purpose Esters of these phenols, especially the benzoic acid and carpentic acid esters, are also therapeutic been applied. When using these esters, however, the inconvenience was emphasized and described from different quarters. that they can only be split with difficulty and imperfectly in the organism, and hence the intended action of guaiacol or eugenol do not bring it to full advantage. This problem can and will be completely eliminated Bodies of valuable therapeutic properties obtained by introducing a Amido group in para position in the acid residue of the esters mentioned.
Zur Darstellung dieser p-Amidobenzoesäureester des Guajacols und Eugenols benutzt man als Ausgangsmaterial am vortheilhaftesten die ρ - Nitrobenzoesäure. Das Guajacol bezw. Eugenol wird mit so viel Kali- oder Natronlauge versetzt, dafs der Hydroxylwasserstoff derselben durch Kalium oder Natrium vollständig substituirt ist. Das Kalium- bezw. Natriumsalz der betreffenden Phenole kann entweder zunächst durch Ümkrystallisiren aus Alkohol gereinigt oder mit gleich technischem Erfolge sogleich mit der zur Bindung des in ihm enthaltenen Alkalimetalls an Chlor erforderlichen äquivalenten Menge des aus der ρ-Nitrobenzoesäure durch Einwirkung von Phosphorpentachlorid hergestellten p-Nitrobenzoylchlorids versetzt werden. Mit gleich technischem Erfolge kann man auch an Stelle des eben erwähnten Chlorids das p-Nitrobenzoe'säureanhydrid verwenden. Die beim Zusammenbringen der Stoffe entstehende Erwärmung reicht meistens hin, um die Reation z. B. im Sinne folgender GleichungThese p-amidobenzoic acid esters of guaiacol and eugenol are used to prepare The most advantageous starting material is ρ-nitrobenzoic acid. The guaiacol respectively. Eugenol is mixed with so much potassium hydroxide or sodium hydroxide solution that the hydroxyl hydrogen is added it is completely substituted by potassium or sodium. The potassium or The sodium salt of the phenols in question can either initially be removed by crystallization Alcohol purified or with the same technical success immediately with the binding of the in it contains alkali metal of chlorine equivalent amount of the required from the ρ-nitrobenzoic acid p-nitrobenzoyl chloride produced by the action of phosphorus pentachloride be moved. With the same technical success you can also take the place of the chloride just mentioned use p-nitrobenzoic anhydride. The warming that occurs when the substances are brought together is usually sufficient to reduce the reaction z. B. in the sense of the following equation
C1. H. C „C 1 . H. C "
C*Hi\CO~Cl= r π 70 +NaCl C * H i \ CO ~ Cl = r π 70 + NaCl
Guajacolnatrium ρ - NitrobenzoylchloridSodium guaiacol ρ - nitrobenzoyl chloride
0 C H3 0 CH 3
ρ -Nitrobenzoylguajacolρ -nitrobenzoylguaiacol
2.2.
C HC H
/- ο/ - ο
^ ONa^ ONa
^2 ^ 2
O Cl —O Cl -
4 \ C O 4 \ CO
O +NaClO + NaCl
Eugenolnatrram ρ-NitrobenzoylchloridEugenol sodium ρ-nitrobenzoyl chloride
ρ - Nitrobenzoyleugenolρ - nitrobenzoyleugenol
zwischen den Körpern zu vollziehen; im anderen Fall erwärmt man auf dem Wasserbade. Das ρ - Nitrobenzoylguajacol bezw. p-Nitrobenzoyleugenol scheidet sich als gelbes OeI ab und erstarrt nach dem Erkalten krystallinisch. to perform between the bodies; in the other case one warms up on the water bath. The ρ - Nitrobenzoylguajacol respectively. p-Nitrobenzoyleugenol separates as a yellow one OeI and solidifies crystalline after cooling.
Die Producte werden durch Auswaschen mit heifsem Wasser von Chlornatrium befreit und sodann aus Alkohol umkrystallisirt. Sie bilden schwach gelb gefärbte Körper, deren Charakterisirung weiter unten erfolgt.The products are freed from sodium chloride by washing them out with hot water then recrystallized from alcohol. They form bodies, pale yellow in color, which characterize them takes place below.
Man kann diese p-Nitrobenzoesäurephenolester auch erhalten, indem man auf ein Gemisch des Phenols oder deren Kalium- bezw. Natriumverbindungen und p-Nitrobenzoesäure bezw. deren Salze Phosphorpentachlorid (P Cl5), Phosphoroxychlorid (P O Cl3), Kohlenoxychlorid (C O Cl2), Sulfurylchlorid (S O2 Cl2) oder saure schwefelsaure Alkalien einwirken läfst.This p-nitrobenzoic acid phenol ester can also be obtained by reacting on a mixture of the phenol or its potassium or potassium. Sodium compounds and p-nitrobenzoic acid respectively. the salts of which are phosphorus pentachloride (P Cl 5 ), phosphorus oxychloride (PO Cl 3 ), carbon oxychloride (CO Cl 2 ), sulfuryl chloride (S O 2 Cl 2 ) or acidic sulfuric acid alkalis.
Die so gewonnenen ρ - Nitrobenzoesäurephenolester werden nunmehr durch Reduction in die entsprechenden Amidoverbindungen, in p-Amidobenzoylguajacol der FormelThe ρ-nitrobenzoic acid phenol esters obtained in this way are now reduced to the corresponding amido compounds, in p-amidobenzoylguajacol of the formula
C6H/- OCH3 C 6 H / - OCH 3
und p-Amidobenzoyleugenol der Formeland p-amidobenzoyleugenol of the formula
C O C O
Cf H3- O C H,Cf H 3 - OCH,
UOv *»UOv * »
übergeführt. Diese Reduction hat sehr vorsichtig zu geschehen, da bei Anwendung stark reducirender Mittel ein Zerfall des Molecüls zu befürchten ist. Von den bekannten Reductionsmitteln Zinn oder Eisen und Salzsäure oder Essigsäure, oder ferner Zinnchlorür und Salzsäure, oder endlich Schwefelammon erweist sich das letztere für den vorliegenden Zweck zur Reduction am geeignetsten.convicted. This reduction has to be done very carefully because it is strong when used reducing agent a disintegration of the molecule is to be feared. Of the known reducing agents Tin or iron and hydrochloric acid or acetic acid, or furthermore tin chloride and hydrochloric acid, or finally, ammonium sulphide turns out to be the latter for the present purpose Reduction most suitable.
Werden die p-Nitrobenzoylphenole mit Schwefelammonlösung schwach erwärmt, so beginnen nach schon kurzer Einwirkung die betreffenden Amidoverbindungen sich in weifser Form auszuscheiden und können durch Umkrystallisiren aus Alkohol gereinigt werden.If the p-nitrobenzoylphenols are warmed slightly with sulfur ammonium solution, so After a short period of exposure, the amido compounds in question begin to turn white Form and can be purified by recrystallizing from alcohol.
Bringt man das so erhaltene ρ - Amidobenzoylguajacol und das p-Amidobenzoyleugenol mit Essigsäureanhydrid zusammen, so findet zunächst langsame Lösung und hierauf eine krystallinische Ausscheidung statt. Die ausgeschiedenen Körper, das p-Acetamidobenzoylguajacol Bring the ρ-amidobenzoylguajacol and p-amidobenzoyleugenol obtained in this way with you Acetic anhydride together, it first finds a slow solution and then a crystalline excretion takes place. The excreted body, the p-acetamidobenzoylguaiacol
NH- COCH3 NH-COCH 3
C6H^OCH3 C 6 H ^ OCH 3
beziehentlich das p-Acetamidobenzoyleugenol
r π /NH- COCH3 referring to the p-acetamidobenzoyleugenol
r π / NH- COCH 3
\
X \
X
C6HXo CHt C 6 HXo CH t
lassen sich durch Umkrystallisiren aus Alkohol reinigen. Sie sind gleich den nichtacetylirten p-Amidobenzoesäureestern im Organismus leicht spaltbar und für die Therapeutik in dem oben erwähnten Sinne von grofsem Werth.can be purified by recrystallization from alcohol. They are like the non-acetylated p-Amidobenzoic acid esters easily cleavable in the organism and for the therapeutics in the above mentioned senses of great value.
Charakterisirung der nach vorstehend beschriebenem Verfahren erhaltenenCharacterization of those obtained by the process described above
neuen Körper.new body.
ι. ρ-Nitrobenzoylguajacol bildet schwach gelb gefärbte, derbe, spiefsige harte Krystalle, welche in Wasser kaum löslich sind und von Aether, Chloroform, Aceton, heifsem Alkohol leicht gelöst werden. Der Schmelzpunkt der Krystalle liegt bei 101 bis 1020, beim Erwärmen mit alkoholischer Kalilauge tritt Spaltung in p-Nitrobenzoesäure und Guajacol ein, dessen Geruch sich sodann bemerkbar macht.ι. ρ-Nitrobenzoylguaiacol forms pale yellow colored, coarse, spongy, hard crystals, which are hardly soluble in water and are easily dissolved by ether, chloroform, acetone, and hot alcohol. The melting point of the crystals is 101 to 102 0 , when heated with alcoholic potassium hydroxide solution, cleavage occurs into p-nitrobenzoic acid and guaiacol, the odor of which is then noticeable.
2. p-Amidobenzoylguajacol bildet einen amorphen, weifsen Körper oder, aus Alkohol krystallisirt, farblose, nadeiförmige verfilzte Krystalle vom Schmelzpunkt 1450; Löslichkeitsverhältnisse und sonstige Eigenschaften wie unter 1.2. p-Amidobenzoylguajacol forms an amorphous body or whites, crystallizes from alcohol, colorless, matted acicular crystals of melting point 145 0; Solubility ratios and other properties as under 1.
3. p-Acetamidobenzoylguajacol bildet farblose, bei 1790 schmelzende Krystalle, welche sich am Licht färben.3. p-Acetamidobenzoylguajacol forms colorless, at 179 0-melting crystals, which stain on the light.
4. p-Nitrobenzoyleugenol bildet schwäch gelb gefärbte, glänzende prismatische Krystalle vom Schmelzpunkt 80,5°; Lösungsverhältnisse und sonstige Eigenschaften wie unter 1.4. p-Nitrobenzoyleugenol forms pale yellow colored, shiny prismatic crystals of melting point 80.5 °; Solution ratios and other properties as under 1.
5. p-Amidobenzoyleugenol bildet lockere Krystallblättchen vom Schmelzpunkt 1560.5. p-Amidobenzoyleugenol forms loose Krystallblättchen of melting point 156 0th
6. p-Acetamidobenzoyleugenol krystallisirt in nahezu farblosen Nadeln vom Schmelzpunkt 160 bis 161 °.6. p-Acetamidobenzoyleugenol crystallizes in almost colorless needles with a melting point 160 to 161 °.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE67923C true DE67923C (en) |
Family
ID=341503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT67923D Expired - Lifetime DE67923C (en) | Process for the preparation of the p-amidobenzoic acid esters of guaiacol and eugenol, as well as the acetyl derivatives of these esters |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE67923C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2466458A1 (en) * | 1979-09-27 | 1981-04-10 | Mathieu Andre | NEW EUGENOL-DERIVED MEDICINAL PRODUCTS |
-
0
- DE DENDAT67923D patent/DE67923C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2466458A1 (en) * | 1979-09-27 | 1981-04-10 | Mathieu Andre | NEW EUGENOL-DERIVED MEDICINAL PRODUCTS |
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